Methyl iodide → HCID 59787348, compound

HRID 1965972Notes

Reaction equation

HRID 1965972 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:20]3[NH:21][N:22]=[N:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:31](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[C:15]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:22]([CH3:31])[N:21]=3)=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178451589HCID 178451589, compound

Product 1

HCID 59787348HCID 59787348, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-(5-phenyl-3H-[1,2,3]triazol-4-yl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (24 mg, 0.06 mmol) in acetone (1.4 mL). Add potassium carbonate (41 mg, 0.3 mmol) and iodomethane (7.4 μL, 0.12 mmol) and stir for 16 h at room temperature. Filter the mixture through a fritted glass funnel and evaporate the filtrate. Purify the crude mixture by chromatography on silica gel to obtain the desired intermediate as the first of the three methylation isomers (7.8 mg, 25%).

Workup

  1. filtrationFilter the mixture through a fritted glass funnel
  2. customevaporate the filtrate
  3. customPurify the crude mixture by chromatography on silica gel

Sources & evidence

ORD record
ord-f43fbb959eba41a19bff4777eb1ad286
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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